NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	263.425
LogP:	3.52
LogD:	3.145
LogS:	-3.059
# Rotatable Bonds:	0
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.744
Synthetic Accessibility Score:	4.374
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.7
MDCK Permeability:	2.435545320622623e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.938
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.332
Plasma Protein Binding (PPB):	92.07967376708984%
Volume Distribution (VD):	3.223
Pgp-substrate:	13.788434982299805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.387
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.554
CYP2C9-inhibitor:	0.25
CYP2C9-substrate:	0.48
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.499
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	17.207
Half-life (T1/2):	0.457

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.914
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.361
Carcinogencity:	0.956
Eye Corrosion:	0.012
Eye Irritation:	0.08
Respiratory Toxicity:	0.966

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC250075

Natural Product ID:	NPC250075
*Common Name:**	Dendocarbin B
IUPAC Name:	(5aS,8S,9aS,9bR)-8-hydroxy-6,6,9a-trimethyl-5,5a,7,8,9,9b-hexahydro-3H-benzo[g][2]benzofuran-1-one
Synonyms:
Standard InCHIKey:	LBTUETJAZNSVAD-OHTBPHCPSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-14(2)6-10(16)7-15(3)11(14)5-4-9-8-18-13(17)12(9)15/h4,10-12,16H,5-8H2,1-3H3/t10-,11-,12+,15-/m0/s1
SMILES:	O[C@H]1CC(C)(C)[C@H]2[C@@](C1)(C)[C@H]1C(=O)OCC1=CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470687
PubChem CID:	10879534
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO8660	Dendrodoris carbunculosa	Species	Dendrodorididae	Eukaryota	n.a.	Amatsu-kominato, Boso Peninsula, central Japan (35 07N, 140 11E)	1999-NOV	PMID[11421732]
NPO7781	Piper scutifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18031016]
NPO6857	Actinidia eriantha	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8660	Dendrodoris carbunculosa	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO578	Eriope blanchetii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2429	Gracilariopsis lemaneiformis	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7781	Piper scutifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7474	Sicya macularia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7919	Hedysarum sericeum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5987	Hypericum yojiroanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6857	Actinidia eriantha	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1548	Nardia succulenta	Species	Solenostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24628	Lamium galeobdolon	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5268	Chenopodium hircinum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	11.5	ug.mL-1	PMID[508238]
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.2	ug.mL-1	PMID[508238]
NPT168	Cell Line	P388	Mus musculus	IC50	=	9.0	ug.mL-1	PMID[508238]
NPT168	Cell Line	P388	Mus musculus	IC50	=	7.0	ug.mL-1	PMID[508238]
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.5	ug.mL-1	PMID[508238]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC250075 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1042
0.2-0.3	3839
0.3-0.4	7537
0.4-0.5	14081
0.5-0.6	6500
0.6-0.7	6710
0.7-0.8	2646
0.8-0.85	151
0.85-0.9	19
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9213	High Similarity	NPC158488
0.914	High Similarity	NPC23364
0.8969	High Similarity	NPC469607
0.8936	High Similarity	NPC216478
0.8901	High Similarity	NPC186363
0.8901	High Similarity	NPC233345
0.8878	High Similarity	NPC110496
0.8854	High Similarity	NPC273005
0.8854	High Similarity	NPC31058
0.8854	High Similarity	NPC469606
0.8817	High Similarity	NPC183012
0.8788	High Similarity	NPC275539
0.8788	High Similarity	NPC189075
0.8764	High Similarity	NPC6979
0.8764	High Similarity	NPC250981
0.8763	High Similarity	NPC36688
0.8681	High Similarity	NPC116620
0.8673	High Similarity	NPC258532
0.8652	High Similarity	NPC52628
0.8636	High Similarity	NPC470948
0.8632	High Similarity	NPC474343
0.8587	High Similarity	NPC152467
0.8586	High Similarity	NPC127609
0.8571	High Similarity	NPC277771
0.8557	High Similarity	NPC471412
0.8556	High Similarity	NPC329692
0.8539	High Similarity	NPC97505
0.8506	High Similarity	NPC195424
0.85	High Similarity	NPC230541
0.8478	Intermediate Similarity	NPC168131
0.8454	Intermediate Similarity	NPC471413
0.8454	Intermediate Similarity	NPC47024
0.8447	Intermediate Similarity	NPC194951
0.8447	Intermediate Similarity	NPC12046
0.8444	Intermediate Similarity	NPC110405
0.8421	Intermediate Similarity	NPC316215
0.8421	Intermediate Similarity	NPC90014
0.8416	Intermediate Similarity	NPC89171
0.8416	Intermediate Similarity	NPC476802
0.8404	Intermediate Similarity	NPC475657
0.8404	Intermediate Similarity	NPC147272
0.84	Intermediate Similarity	NPC478208
0.8387	Intermediate Similarity	NPC232202
0.8384	Intermediate Similarity	NPC474775
0.8384	Intermediate Similarity	NPC254202
0.837	Intermediate Similarity	NPC477128
0.8365	Intermediate Similarity	NPC157441
0.8333	Intermediate Similarity	NPC165528
0.8333	Intermediate Similarity	NPC29952
0.8333	Intermediate Similarity	NPC141350
0.8333	Intermediate Similarity	NPC228766
0.8316	Intermediate Similarity	NPC225474
0.8316	Intermediate Similarity	NPC57117
0.8316	Intermediate Similarity	NPC469596
0.8316	Intermediate Similarity	NPC148000
0.8315	Intermediate Similarity	NPC178676
0.8298	Intermediate Similarity	NPC49420
0.8298	Intermediate Similarity	NPC477574
0.8283	Intermediate Similarity	NPC162973
0.8283	Intermediate Similarity	NPC476081
0.8283	Intermediate Similarity	NPC137430
0.8283	Intermediate Similarity	NPC295791
0.8283	Intermediate Similarity	NPC58329
0.8283	Intermediate Similarity	NPC235369
0.828	Intermediate Similarity	NPC474396
0.828	Intermediate Similarity	NPC50488
0.828	Intermediate Similarity	NPC73995
0.8276	Intermediate Similarity	NPC35574
0.8265	Intermediate Similarity	NPC476767
0.8265	Intermediate Similarity	NPC472644
0.8261	Intermediate Similarity	NPC181103
0.8261	Intermediate Similarity	NPC312561
0.8261	Intermediate Similarity	NPC305029
0.8252	Intermediate Similarity	NPC5103
0.8247	Intermediate Similarity	NPC70145
0.8247	Intermediate Similarity	NPC91695
0.8247	Intermediate Similarity	NPC285513
0.8247	Intermediate Similarity	NPC254496
0.8235	Intermediate Similarity	NPC476479
0.8229	Intermediate Similarity	NPC157686
0.8229	Intermediate Similarity	NPC259042
0.8222	Intermediate Similarity	NPC22611
0.8218	Intermediate Similarity	NPC252296
0.8218	Intermediate Similarity	NPC102352
0.8211	Intermediate Similarity	NPC166346
0.8211	Intermediate Similarity	NPC99653
0.8202	Intermediate Similarity	NPC473420
0.82	Intermediate Similarity	NPC99266
0.82	Intermediate Similarity	NPC8196
0.82	Intermediate Similarity	NPC120321
0.8191	Intermediate Similarity	NPC153853
0.819	Intermediate Similarity	NPC312017
0.819	Intermediate Similarity	NPC25909
0.819	Intermediate Similarity	NPC9848
0.8182	Intermediate Similarity	NPC81530
0.8182	Intermediate Similarity	NPC475958
0.8173	Intermediate Similarity	NPC469655
0.8173	Intermediate Similarity	NPC469656
0.8173	Intermediate Similarity	NPC474846
0.8173	Intermediate Similarity	NPC188738
0.8172	Intermediate Similarity	NPC215831
0.8163	Intermediate Similarity	NPC234617
0.8163	Intermediate Similarity	NPC476806
0.8163	Intermediate Similarity	NPC476807
0.8163	Intermediate Similarity	NPC124703
0.8155	Intermediate Similarity	NPC474243
0.8155	Intermediate Similarity	NPC143706
0.8155	Intermediate Similarity	NPC472534
0.8155	Intermediate Similarity	NPC478210
0.8152	Intermediate Similarity	NPC85698
0.8152	Intermediate Similarity	NPC477920
0.8152	Intermediate Similarity	NPC471219
0.8152	Intermediate Similarity	NPC473226
0.8144	Intermediate Similarity	NPC284518
0.8144	Intermediate Similarity	NPC11396
0.8144	Intermediate Similarity	NPC21302
0.8144	Intermediate Similarity	NPC202833
0.8144	Intermediate Similarity	NPC93245
0.8144	Intermediate Similarity	NPC234993
0.8144	Intermediate Similarity	NPC134072
0.8137	Intermediate Similarity	NPC144854
0.8137	Intermediate Similarity	NPC3316
0.8137	Intermediate Similarity	NPC184512
0.8131	Intermediate Similarity	NPC98249
0.8131	Intermediate Similarity	NPC473590
0.8131	Intermediate Similarity	NPC53396
0.8131	Intermediate Similarity	NPC469684
0.8125	Intermediate Similarity	NPC470957
0.8125	Intermediate Similarity	NPC471720
0.8125	Intermediate Similarity	NPC24861
0.8125	Intermediate Similarity	NPC470958
0.8119	Intermediate Similarity	NPC296950
0.8119	Intermediate Similarity	NPC222161
0.8105	Intermediate Similarity	NPC475972
0.8105	Intermediate Similarity	NPC124374
0.8105	Intermediate Similarity	NPC72845
0.8105	Intermediate Similarity	NPC234335
0.81	Intermediate Similarity	NPC471363
0.81	Intermediate Similarity	NPC164551
0.81	Intermediate Similarity	NPC238397
0.81	Intermediate Similarity	NPC136289
0.81	Intermediate Similarity	NPC476769
0.81	Intermediate Similarity	NPC165250
0.8095	Intermediate Similarity	NPC269530
0.8095	Intermediate Similarity	NPC126691
0.8095	Intermediate Similarity	NPC476801
0.8085	Intermediate Similarity	NPC261320
0.8085	Intermediate Similarity	NPC5509
0.8085	Intermediate Similarity	NPC194642
0.8085	Intermediate Similarity	NPC246028
0.8081	Intermediate Similarity	NPC472972
0.8081	Intermediate Similarity	NPC476299
0.8081	Intermediate Similarity	NPC474012
0.8081	Intermediate Similarity	NPC117685
0.8081	Intermediate Similarity	NPC476274
0.8077	Intermediate Similarity	NPC478209
0.8077	Intermediate Similarity	NPC478211
0.8065	Intermediate Similarity	NPC470012
0.8065	Intermediate Similarity	NPC175293
0.8061	Intermediate Similarity	NPC17326
0.8061	Intermediate Similarity	NPC473963
0.8061	Intermediate Similarity	NPC134454
0.8058	Intermediate Similarity	NPC277017
0.8058	Intermediate Similarity	NPC154608
0.8058	Intermediate Similarity	NPC192813
0.8056	Intermediate Similarity	NPC284707
0.8041	Intermediate Similarity	NPC37603
0.8041	Intermediate Similarity	NPC471786
0.8041	Intermediate Similarity	NPC134067
0.8022	Intermediate Similarity	NPC105173
0.8021	Intermediate Similarity	NPC139692
0.8021	Intermediate Similarity	NPC474436
0.8021	Intermediate Similarity	NPC63118
0.8021	Intermediate Similarity	NPC477855
0.8021	Intermediate Similarity	NPC470224
0.8021	Intermediate Similarity	NPC115021
0.8021	Intermediate Similarity	NPC49776
0.802	Intermediate Similarity	NPC7644
0.802	Intermediate Similarity	NPC474165
0.802	Intermediate Similarity	NPC69171
0.802	Intermediate Similarity	NPC134270
0.802	Intermediate Similarity	NPC7613
0.802	Intermediate Similarity	NPC475321
0.802	Intermediate Similarity	NPC140723
0.802	Intermediate Similarity	NPC159442
0.802	Intermediate Similarity	NPC127933
0.802	Intermediate Similarity	NPC475889
0.802	Intermediate Similarity	NPC159533
0.802	Intermediate Similarity	NPC476237
0.802	Intermediate Similarity	NPC275583
0.8019	Intermediate Similarity	NPC469454
0.8019	Intermediate Similarity	NPC469463
0.8019	Intermediate Similarity	NPC469496
0.8	Intermediate Similarity	NPC132790
0.8	Intermediate Similarity	NPC472643
0.8	Intermediate Similarity	NPC469595
0.8	Intermediate Similarity	NPC223330
0.8	Intermediate Similarity	NPC97435
0.8	Intermediate Similarity	NPC247031
0.8	Intermediate Similarity	NPC100329

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC250075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1333
0.2-0.3	3618
0.3-0.4	2542
0.4-0.5	939
0.5-0.6	270
0.6-0.7	261
0.7-0.8	42
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.798	Intermediate Similarity	NPD7638	Approved
0.79	Intermediate Similarity	NPD7640	Approved
0.79	Intermediate Similarity	NPD7639	Approved
0.7849	Intermediate Similarity	NPD1694	Approved
0.7653	Intermediate Similarity	NPD6399	Phase 3
0.7653	Intermediate Similarity	NPD5779	Approved
0.7653	Intermediate Similarity	NPD5778	Approved
0.7624	Intermediate Similarity	NPD4225	Approved
0.7527	Intermediate Similarity	NPD3667	Approved
0.7524	Intermediate Similarity	NPD6008	Approved
0.7396	Intermediate Similarity	NPD3618	Phase 1
0.7374	Intermediate Similarity	NPD6411	Approved
0.7368	Intermediate Similarity	NPD4786	Approved
0.7347	Intermediate Similarity	NPD5328	Approved
0.734	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6053	Discontinued
0.7248	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7632	Discontinued
0.7228	Intermediate Similarity	NPD7748	Approved
0.7222	Intermediate Similarity	NPD6686	Approved
0.72	Intermediate Similarity	NPD7515	Phase 2
0.72	Intermediate Similarity	NPD6079	Approved
0.7196	Intermediate Similarity	NPD6675	Approved
0.7196	Intermediate Similarity	NPD7128	Approved
0.7196	Intermediate Similarity	NPD6402	Approved
0.7196	Intermediate Similarity	NPD5739	Approved
0.7184	Intermediate Similarity	NPD7902	Approved
0.7172	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6101	Approved
0.7168	Intermediate Similarity	NPD7115	Discovery
0.7156	Intermediate Similarity	NPD6373	Approved
0.7156	Intermediate Similarity	NPD6372	Approved
0.713	Intermediate Similarity	NPD5701	Approved
0.713	Intermediate Similarity	NPD5697	Approved
0.7113	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4697	Phase 3
0.7064	Intermediate Similarity	NPD7320	Approved
0.7064	Intermediate Similarity	NPD6881	Approved
0.7064	Intermediate Similarity	NPD6011	Approved
0.7064	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6899	Approved
0.7054	Intermediate Similarity	NPD4632	Approved
0.7041	Intermediate Similarity	NPD5330	Approved
0.7041	Intermediate Similarity	NPD6409	Approved
0.7041	Intermediate Similarity	NPD7146	Approved
0.7041	Intermediate Similarity	NPD6684	Approved
0.7041	Intermediate Similarity	NPD7521	Approved
0.7041	Intermediate Similarity	NPD7334	Approved
0.7027	Intermediate Similarity	NPD6650	Approved
0.7027	Intermediate Similarity	NPD6649	Approved
0.701	Intermediate Similarity	NPD3665	Phase 1
0.701	Intermediate Similarity	NPD3666	Approved
0.701	Intermediate Similarity	NPD3133	Approved
0.7	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.6975	Remote Similarity	NPD7507	Approved
0.6972	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3573	Approved
0.6939	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7290	Approved
0.6937	Remote Similarity	NPD7102	Approved
0.6937	Remote Similarity	NPD6883	Approved
0.6931	Remote Similarity	NPD46	Approved
0.6931	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8515	Approved
0.6923	Remote Similarity	NPD8516	Approved
0.6923	Remote Similarity	NPD5221	Approved
0.6923	Remote Similarity	NPD8517	Approved
0.6923	Remote Similarity	NPD5222	Approved
0.69	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6903	Approved
0.6893	Remote Similarity	NPD7900	Approved
0.6893	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8130	Phase 1
0.6875	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6617	Approved
0.6875	Remote Similarity	NPD6869	Approved
0.6875	Remote Similarity	NPD6847	Approved
0.687	Remote Similarity	NPD6009	Approved
0.6863	Remote Similarity	NPD7637	Suspended
0.6863	Remote Similarity	NPD8034	Phase 2
0.6863	Remote Similarity	NPD8035	Phase 2
0.6857	Remote Similarity	NPD6083	Phase 2
0.6857	Remote Similarity	NPD4755	Approved
0.6857	Remote Similarity	NPD5173	Approved
0.6857	Remote Similarity	NPD6084	Phase 2
0.6838	Remote Similarity	NPD6319	Approved
0.6837	Remote Similarity	NPD3668	Phase 3
0.6832	Remote Similarity	NPD1695	Approved
0.6827	Remote Similarity	NPD5695	Phase 3
0.6814	Remote Similarity	NPD8297	Approved
0.6814	Remote Similarity	NPD6882	Approved
0.6803	Remote Similarity	NPD7319	Approved
0.6796	Remote Similarity	NPD4202	Approved
0.6792	Remote Similarity	NPD5696	Approved
0.678	Remote Similarity	NPD5983	Phase 2
0.6774	Remote Similarity	NPD8039	Approved
0.6765	Remote Similarity	NPD5785	Approved
0.6759	Remote Similarity	NPD5211	Phase 2
0.675	Remote Similarity	NPD7492	Approved
0.6733	Remote Similarity	NPD5737	Approved
0.6733	Remote Similarity	NPD6672	Approved
0.6729	Remote Similarity	NPD5286	Approved
0.6729	Remote Similarity	NPD4700	Approved
0.6729	Remote Similarity	NPD4696	Approved
0.6729	Remote Similarity	NPD5285	Approved
0.6724	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5279	Phase 3
0.67	Remote Similarity	NPD5786	Approved
0.6699	Remote Similarity	NPD7983	Approved
0.6699	Remote Similarity	NPD5693	Phase 1
0.6696	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6059	Approved
0.6695	Remote Similarity	NPD6054	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD8293	Discontinued
0.6639	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7078	Approved
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD8074	Phase 3
0.6639	Remote Similarity	NPD6016	Approved
0.6638	Remote Similarity	NPD6868	Approved
0.6638	Remote Similarity	NPD6274	Approved
0.6637	Remote Similarity	NPD6371	Approved
0.6636	Remote Similarity	NPD5141	Approved
0.6634	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD8133	Approved
0.6606	Remote Similarity	NPD5225	Approved
0.6606	Remote Similarity	NPD5224	Approved
0.6606	Remote Similarity	NPD5226	Approved
0.6606	Remote Similarity	NPD4633	Approved
0.6602	Remote Similarity	NPD5207	Approved
0.66	Remote Similarity	NPD1696	Phase 3
0.6596	Remote Similarity	NPD7339	Approved
0.6596	Remote Similarity	NPD6942	Approved
0.6585	Remote Similarity	NPD7736	Approved
0.6583	Remote Similarity	NPD6370	Approved
0.6583	Remote Similarity	NPD5988	Approved
0.6581	Remote Similarity	NPD6317	Approved
0.6579	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5282	Discontinued
0.6571	Remote Similarity	NPD6001	Approved
0.6566	Remote Similarity	NPD7154	Phase 3
0.6566	Remote Similarity	NPD5362	Discontinued
0.6562	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7260	Phase 2
0.6557	Remote Similarity	NPD6336	Discontinued
0.6545	Remote Similarity	NPD4754	Approved
0.6545	Remote Similarity	NPD5174	Approved
0.6545	Remote Similarity	NPD5175	Approved
0.6538	Remote Similarity	NPD5284	Approved
0.6538	Remote Similarity	NPD5281	Approved
0.6535	Remote Similarity	NPD6098	Approved
0.6535	Remote Similarity	NPD4519	Discontinued
0.6535	Remote Similarity	NPD4623	Approved
0.6535	Remote Similarity	NPD4249	Approved
0.6525	Remote Similarity	NPD6314	Approved
0.6525	Remote Similarity	NPD6335	Approved
0.6525	Remote Similarity	NPD6313	Approved
0.6518	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5344	Discontinued
0.6505	Remote Similarity	NPD4753	Phase 2
0.65	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7645	Phase 2
0.6491	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD4250	Approved
0.6471	Remote Similarity	NPD7100	Approved
0.6471	Remote Similarity	NPD4251	Approved
0.6471	Remote Similarity	NPD7101	Approved
0.6465	Remote Similarity	NPD4223	Phase 3
0.6465	Remote Similarity	NPD4221	Approved
0.6465	Remote Similarity	NPD6435	Approved
0.6465	Remote Similarity	NPD4270	Approved
0.6465	Remote Similarity	NPD4269	Approved
0.6449	Remote Similarity	NPD7839	Suspended
0.6436	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4767	Approved
0.6429	Remote Similarity	NPD4695	Discontinued
0.6429	Remote Similarity	NPD4768	Approved
0.6421	Remote Similarity	NPD8264	Approved
0.6421	Remote Similarity	NPD3703	Phase 2
0.6408	Remote Similarity	NPD5208	Approved
0.64	Remote Similarity	NPD6695	Phase 3
0.6392	Remote Similarity	NPD6114	Approved
0.6392	Remote Similarity	NPD6697	Approved
0.6392	Remote Similarity	NPD6115	Approved
0.6392	Remote Similarity	NPD6118	Approved
0.6387	Remote Similarity	NPD7327	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data